Abstract
AbstractThe MαNP acid method has been applied to racemic aliphatic acetylene alcohols in order to simultaneously prepare enantiopure alcohols and to determine their absolute configurations by 1H NMR anisotropy. Racemic acetylene alcohols 6–8, 11, and 20 were esterified with MαNP acid (S)‐(+)‐1 to yield diastereomeric MαNP esters which were efficiently separated by HPLC on silica gel with separation factors α in the range 1.60–1.93. The 1H NMR anisotropy factors Δδ [= δ(2nd fr.) – δ(1st fr.)] were calculated from the data of the first‐ (22a–27a) and second‐eluted MαNP esters (22b–27b). The absolute configurations of the first‐eluted esters were determined from the distribution of Δδ values in the MαNP sector rule. In the case of MαNP ester 26b, the assigned absolute configuration was confirmed by X‐ray crystallography. The solvolysis of MαNP esters yielded enantiopure acetylene alcohols 5–8 with established absolute configurations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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